628340-16-9

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 53915-69-8 Prop-2-ynyl(tributyl)stannane 
• 38002-45-8 3-bromo-1-(trimethylsilyl)-1-propyne 
• 108-05-4 vinyl acetate 
• 78808-38-5 1-phenylhexa-4,5-dien-3-ol 
• 53915-69-8 allenyltributylstannane 

Downstream Products

• 1070800-62-2 ((R)-3-methoxyhexa-4,5-dienyl)benzene 

Relevant academic research and scientific papers

Catalytic asymmetric methallylation and propargylation of aldehydes with bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide

New and highly efficient enantioselective methallylation and propargylation of achiral aldehydes with methallyltributyltin and allenyltributyltin, respectively, can be achieved with high enantioselectivity under the influence of chiral bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide as catalyst.

Highly stereoselective kinetic resolution of α-allenic alcohols: An enzymatic approach

A highly efficient lipase AK-catalyzed direct kinetic resolution of a variety of α-allenic alcohols was developed. With the complementary to previous studies, the current reaction system is effective on a broad range of substituents (R1) at C(1), such as alkyl, aryl, alkenyl, and alkynyl groups. The Jones-Burgess empirical model was modified to interpret the reversed selectivity during the acetylation of secondary alcohol. The methyl group at C(2) of allenic alcohols implied a small structural adjustment in the catalytic triad of lipase AK, representing a potential direction for future site-directed mutagenesis.

Studies on the synthesis of durhamycin A: Stereoselective synthesis of a model aglycone

(Chemical Equation Presented) A stereoselective synthesis of the model aglycone corresponding to the anti-HIV aureolic acids durhamycins A (1) and B (2) is described.

Catalytic enantioselective allenylation reactions of aldehydes with tethered bis(8-quinolinolato) (TBOx) chromium complex

The utility of the new class of chiral ligand, tethered bis(8-quinolinol) (TBOxH), is further explored. Its chromium complex, TBOxCr(III)Cl, effectively catalyzes the asymmetric allenylation reactions of various aldehydes at room temperature with high yie

Catalytic asymmetric allylation of aldehydes and related reactions with bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide as a μ-oxo-type chiral Lewis acid

A new, chiral bis-TiIV of type 3 has been designed and can be utilized for strong activation of aldehyde carbonyls, thereby allowing a new catalytic enantioselective allylation of aldehydes with allyltributyltin. The chiral bis-TiIV catalyst (S,S)-3 can be readily prepared either by treatment of bis(triisopropoxy)titanium oxide with (S)-BINOL or by treatment of ((S)-binaphthoxy)isopropoxytitanium chloride with silver(I) oxide. Treatment of hydrocinnamaldehyde with allyltributyltin under the influence of chiral bis-TiIV oxide (S,S)-3 generated in situ (10 mol%) in CH 2Cl2 afforded an allylation product in 84% yield and with 99% ee. This asymmetric allylation with non-racemic bis-TiIV oxide 3 and partially resolved (S)-BINOL shows a positive nonlinear effect in correlation of the enantiopurity of the allylation product with the ee of the (S)-BINOL. Chiral bis-TiIV oxide (S,S)-3 can also be utilized for related reactions such as asymmetric methallylation and propargylation of aldehydes with high enantioselectivity. This asymmetric approach provides a very useful way of obtaining high reactivity and selectivity through the simple introduction of the M-O-M unit into the design of chiral Lewis acid catalysts.

Catalytic asymmetric allenylation: Regulation of the equilibrium between propargyl- and allenylstannanes during the catalytic process

Achiral substrates 1 and 2 can be regioselectively converted into chiral allenyl alcohols 3 through the title reaction [Eq. (1)] with the synergetic reagent iPrSBEt2 and a chiral Ti(IV) catalyst. The dramatic regioselectivity originates from the regulation of the equilibrium between propargyl- and allenylstannanes during the catalytic process.